


Pleasure Slave

by Anonymous



Category: Supernatural
Genre: Activist Castiel (Supernatural), Anal Fingering, Begging Dean, Chastity, Chastity Device, Cock Rings, Cock Tease, Cock Warming, Cuddling & Snuggling, Dom Abaddon, Dom Crowley, Dubious Consent, Edging, Eventual Happy Ending, F/M, Facials, Forced Feminization, Gangbang, Gentle Castiel, Gentle Dom Castiel, Gentle Sex, Hurt/Comfort, John Winchester's A+ Parenting, Lawyer Castiel, M/M, Non-Consensual Spanking, Oral Sex, Orgasm Delay/Denial, Other Additional Tags to Be Added, Overstimulation, Prostate Massage, Public Humiliation, Riding Crops, Sex Slave Dean, Sexual Slavery, Slut Shaming, Sub Dean Winchester, Verbal Humiliation, eventual destiel, tease and denial
Language: English
Status: Completed
Published: 2017-05-01
Updated: 2017-05-04
Packaged: 2018-10-26 12:02:39
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 6
Words: 8,885
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10786383
Author URL: https://archiveofourown.org/
Summary: When Dean was told he would be a pleasure slave, he couldn't believe it.  Obviously, he had no choice but to accept his station, but he never gave up hope on becoming a warrior or a hunter:  a station that was useful, in which he could eventually earn his freedom.Now, it seems he's finally earned his chance to prove himself as a warrior.  Dean is ecstatic.  Unfortunately for him, this involves being shoved in a room with twenty masculine, sexually frustrated beefcakes who look like they could snap him in two.  And it doesn't look like they want to fight.





	1. The Chance

When they'd told Dean he'd be a pleasure slave, he couldn't believe it. Growing up, he'd been absolutely sure he'd be a warrior or a hunter, protecting or performing some useful function. Moreover, if he were a warrior or a hunter, he'd have some chance at earning his freedom: pleasure slaves spent the majority of their youth filling their role, and then they'd typically become caregivers or trainers for other pleasure slaves. It was by no means a life Dean wanted, but it was the one selected for him.

He still remembers the shame when they called his name, all heads turning smugly towards him. Smugly, because that was what everyone had expected of him: they'd insisted he was too pretty to be anything else, and Dean had longed for the day when he could prove them wrong. Now he'd never get the chance to.

He was auctioned off to Crowley shortly afterwards, a poncy British dickbag who wasn't particularly cruel, but delighted in reminding Dean of his station and the indignities that came with it. Sometimes, he even addressed him using female pronouns, called him his "pretty little girl" while Dean sucked him off. Dean, of course, had no say in the matter: he'd been trained to accept any and all of his master's orders, since he was four years old and John had sold him to begin with.

"I don't want to do this, Dean, but you gotta be brave for me," he'd explained, stroking the sobbing child's hair. "Sammy deserves a future, and with your mother gone, I don't know that I could provide it. Not if I had you to worry about. You gotta understand that, Dean."

Dean tried not to dwell on the memory too much.

Aside from that, however, Crowley was never particularly cruel. He provided Dean with a plush dogbed to sleep on and lots of toys, and sometimes, he even let him eat at the table with him. He'd never beat him (unless you counted the occasional spanking), starved him, or mistreated him. He never struck Dean as a particularly cruel master.

Not until now. 

Dean looked down at his lacy pink panties and short, frilly dress, tugging desperately in an attempt to get some more coverage. This had been Crowley's one condition: he had to wear this, in order to fight, to get a chance to prove himself. 

When Crowley had told him, with a completely straight face, that he was going to get a chance to become a warrior, his heart skipped a beat. He'd only half-listened to Crowley's conditions, which of course, revolved around his complete and utter humiliation: he was going to have to go into the warriors' enclosure and fight the strongest he could find, while dressed like this. Crowley, of course, would be there to observe the whole thing for his own amusement. 

"Off you go, buttercup," the British drawl purred in his ear, patting his backside as he was shoved in. 

Inside the room, ten rugged heads turned to look at him, features cracked and scarred and masculine. The warriors were men, twenty-five or older, due to the time consuming training program slaves had to take to become one. They were all muscle, sinuous and rippling, and they looked at Dean with something that first resembled surprise and now turned progressively towards hunger.

Dean, standing there, was fully aware for the first time of how vulnerable he must have appeared. He was eighteen years old, his only fighting experience with other adolescent slaves back at the barracks, comparatively soft and slender and almost effeminate. His only attire was an obscenely short dress and frilly pink underwear, and here he was, confronted with at least ten of the scariest, most manly men he'd ever laid eyes on.

And something told him they didn't want to fight.


	2. The Fight

**Summary for the Chapter:**

> In spite of the impossible odds against him, Dean challenges the warriors' alpha, and realizes belatedly that he may have bitten off a bit more than he can chew.

Dean's trachea contracted as one of the warriors approached, eyeing him up as if he was something for dinner.

"Now what do we have here, huh?" he inquired, beefy arms folded across his bare, scarred chest. "Big Man Crowley finally decide to throw us a bone?" 

He gestured to Crowley, who was still standing outside the barred window to the doorway. He gave a flippant shrug of his shoulders, and if Dean could have fit his fist between the iron bars, he would have decked the smug bastard right then and there.

Instead, Dean forced himself to hold his head high and his shoulders square. This was his chance, and even if the odds of winning were slim, he wasn't going to blow it: if he won, he had a chance to earn his freedom. In fifteen years or less, he could be his own person again. He could find little Sammy, meet the person he'd become, see if his sacrifice hadn't been in vain. Maybe by then he'd even have nieces and nephews, some in-laws, a whole family he'd never even known about. He might even be able to see his favorite uncle Bobby again, the one who'd offered to take him in before John sold him.

He couldn't lose that just because Crowley wanted some sick fun at his expense. He couldn't.

"I'm Dean Winchester," he said, impressed by how steady he kept his voice. "And I'm here to fight the strongest warrior you have."

There was a brief silence, before the warriors erupted into laughter. Dean felt a flush blossom from his cheeks all the way to the tips of his ears, a combination of anger and shame as he was reminded how ridiculous he must have appeared. 

"Little princess thinks he's a warrior," someone hooted. 

"I'm not even sure he's a 'he!'" chimed in another.

Dean was fuming. "Shut up!" he barked. "This, this wasn't my idea, alright? I wanted to become a warrior and this is the only way I could do it, so you can all just kiss my -" 

"Oh, so you wanna be a *warrior,*" said the scarred warrior, who Dean presumed to be their alpha. He drawled the last word out, as though he was humoring a child. "Lemme guess. You're a pleasure slave, right?"

"No," said Dean, on reflex. The warrior cocked his eyebrows, and he elaborated, "I mean, I am for *now.* But just because what the dumbass comity back at the barracks picked for me. I was supposed to be a warrior, or a hunter at least." 

The warrior tapped his chin, lip jutted thoughtfully. "Naw. Nawnawnaw, kid, you're a pleasure slave if I ever seen one. I mean, c'mon. Face like that?" he chuckled, reaching out to brush Dean's cheek with his fingertips. "You're too pretty to be anything else."

The familiar comment had red-hot rage boiling up inside of Dean. It brought back everything every dick back at the barracks had ever said to him, Allistaire and Meg Masters and Azazel. Even his eventual trainer -- and of course, former pleasure slave -- Abaddon had made similar remarks. 

"Shut up and fight me, you fucking bitch!" Dean shouted, flinging himself at the stationary warrior.

This rage-fueled attack proved to be a foolish one, especially because the warrior topped Dean by a solid four inches and a good fifty-or-so pounds. In at least his late thirties, he obviously had a similar edge of experience. 

The warrior easily deflected Dean's attack, catching him by the wrist and steering him away. "Woah, princess!" he laughed. "You said you wanted to fight the toughest we got, right? Well, much as it pains me to admit it, that ain't me." 

Dean blinked, eyes narrowing suspiciously at his would-be foe. "It...it 'ain't?'"

"Naw, I'm just the beta," he shrugged. "The face of the production, you might say. That back there," he continued, pointing towards the back of the room. "Is the alpha."

The crowd of grinning warriors cleared a path, hooting and cackling as Dean's eyes went round. 

Sitting at the back of the room was the largest person Dean had ever seen. He sat with his arms crossed and his feet planted wide, each limb as thick as a tree trunk. As he slowly got to his feet, Dean's heart sank at the height of him: he must have been over six-and-a-half-feet-tall! 

The warrior approached, grinning a yellow, crack-toothed grin, bald head scarred and one eye milky. His ears were lined with piercings, an ugly gash of a scar extenuating over his blind eye and down his prickly jaw. "You ready to dance, pretty thing?" he asked, voice a deep baritone. 

Dean swallowed, hands instinctively clutching at the lacy fabric of the ridiculous, humiliating dress Crowley had forced him to wear. He'd been made to crossdress in public before, of course -- for a pleasure slave, particularly a male one, it wasn't at all rare -- but it was something about this situation that made it all the worse. He wanted to defeat the warriors, he realized, but he also wanted their respect. He wanted to be seen as being on their level. 

Now, decked out as he was, it made the power imbalance all the more glaring. 

There was no way he could do this, he thought. But he remembered Sammy, the baby brother he'd slept with every night after his mother's death, the milky smell of his fuzzy head. He remembered his Uncle Bobby, the only one who'd dared speak in Dean's defense when John had decided to sell him into slavery. He remembered being free, cuddling with his Mom at night and eating at the table every evening, with a fork and a knife and a cup instead of a bowl, like a human being. He remembered that if he didn't win now, he might never get those things back. 

So he stepped back, looking the alpha over for possible weaknesses: his size might be one, Dean reasoned, noting the way his potbelly hung over the belt of his pants. His blind eye was another. If Dean used his agility and stuck to the alpha's blind side, he might win. 

"Yeah," Dean growled, upper lip curling. "Lets dance." 

The alpha didn't have a chance to react as Dean dashed around his blind side, wrapping his arm around the tree trunk of his bicep and using the free one to punch him in the kidney with all his might, once, twice, and then three times. 

To his dismay, he didn't get much of an effect from the alpha except for a stiffening and a low grunt, and when he glanced up to see if his ministrations had had any effect at all, he felt the alpha wrap his arm around Dean's head, getting him into an inescapable hold.

"Had to have that one removed after a spear got me there," the alpha explained with a chuckle. "Mind the scar." 

"Let me go you fuckin' freak," Dean grunted, thrashing around in his hold.

"Sure thing, princess." 

The warriors let out a unanimous whoop as the alpha smacked his lace-covered backside, Dean's face flushed from the exertion and the indignity as he was finally let go. That, in his opinion, only made it worse: this was just a game to the alpha, not a legitimate fight. Nevertheless, Dean refused to give up, more determined than ever to make everyone eat their words. 

He surged forward without warning, kneeing the alpha in the crotch. This did garner some effect, the alpha letting out a surprised, "Oof!" and doubling over somewhat, just enough for Dean's fist to shoot upwards and collide with his nose, the satisfying *CRACK!* it yielded enough to let him know he'd bloodied it. A surprised murmur even regurgitated throughout the warriors as Dean jumped backwards to avoid the alpha's reflexively swinging fist. 

He couldn't help but smirk to himself: so all the fight's he'd gotten into back at the barracks hadn't been a waste after all.

Dean's victory was short-lived, however, as he felt the warrior's fingers knotting in his short hair and dragging him forwards, the alpha's eyes full of rage and a rivulet of purple blood trickling from one nostril. Dean preemptively swung his fists, but both were caught in the alpha's free hand, and he spun him around, so that he was faced backwards, his back pressed to the alpha's chest and held there with the alpha's free arm. 

Dean struggled with all his might wriggling like a worm in the alpha's hold, but in that moment, he -- and everyone else present -- knew that he'd been beat. 

He looked desperately out over the crowd of overexcited warriors, to where Crowley's smug face still watched him from the door. He hated all of them. He hated them for turning him into a trussed-up toy for their pleasure, for never giving a second thought to the fact that he was a child, a little boy, sold against his will by the person supposed to protect him and brought up locked in one cage after another. He hated them for treating him like a two-dimensional object of amusement, never thinking about his feelings or how badly he wanted to be free and home with his family again. 

"I think this little princess needs to be taught some manners, don't you?" the alpha inquired, and the warriors roared their agreement. Dean barely registered. 

His family. He was never going to see them again now, was he? He was never going to see who Sammy had become, if he'd gotten married, if he'd had kids of his own. He'd never see his Uncle Bobby and be able to thank him for sticking up for him, for being more of a father to him than John ever was. He'd never be able to sleep in his own bed, cook his own meals, live in his own house. 

He'd be a slave forever now. 

Dean should have been ashamed when he realized he was crying, but he wasn't. Deep in his soul, he was just tired. His life had ended before it even had a chance to begin. It had ended when he was four years old.

"Awe, don't cry, pretty baby," the alpha crooned mockingly. "We're all gonna take real good care of you, right here and now."

**Notes for the Chapter:**

> This has a happy ending, I swear.


	3. The Punishment

**Summary for the Chapter:**

> The alpha warrior decides to punish a subdued Dean with a harsh spanking.

Dean's footie pajamas scuffed on the ground as he waddled up to the top of the stairs, trying to better hear what Bobby and his dad might be saying. 

"...Look, if he's that much of a burden to you, I'll take the boy in. You know I love that kid like one of my own." 

"It ain't that simple, Singer, and you know it." John's voice had the low drawl to it it always did when he'd just knocked back a whisky. 

"Oh, and why not, huh?"

"For one thing, it's good money. I sell the truck, I MIGHT be able to make the mortgage on a new house. I sell him, I'll be able to make Sam's tuition twice over." 

Dean jolted as he heard someone -- presumably Bobby -- slam his fist down on the table. "DAMMIT, John, this ain't right! Sellin' your own kid, it shouldn't even occur to you as a damn option!"

"Well, maybe it's my only option." 

"Oh, don't gimme that. How about you quit drinkin', huh? How bout you realize that you ain't the only one sufferin' in this, that the boys lost their mother just as much as you lost your wife." Pause. "And y'know, you keep goin' back to Sam, like he's gonna be just THRILLED to grow up and find out, one way or another, that his brother got sold to pay for his diploma. But we know what this is really about, John. You don't want Dean around 'cause he looks too much like Mary! 'Cause you look at his little face, and his blond hair, and you can't help but see her there, can ya?" 

"Shut the fuck up, Singer." 

"They don't get treat well, y'know. Best case scenario, he becomes a warrior or a hunter, provided your genes got any say in it. Them's high value positions right there. He could earn 'is way out in ten years, twenty. He becomes a caregiver, he could be a free man by the time he's forty. But let's say he keeps MARY'S looks, huh? Let's say he grows up to be as pretty as her. Do you really want to go to bed at night, for the rest of your life, knowing that your kid might be a damn pleasure -" 

The words trailed off as Dean crept quickly away, till only the muffled baritone of their voices remained. His little heart pounded in his chest, a hollow in his stomach that wouldn't go away. This didn't seem like it could be real, but somehow, he knew it was.

He didn't want to think about this anymore. He padded quietly back to Sammy's crib and climbed carefully inside, wrapping his arms around the warm, pudgy infant like his personal teddy bear. He scrunched his eyes shut, hoping that if he went to sleep now, what he'd heard might just be a dream.

The next day, Dean was taken to the barracks and sold. 

...

Dean stifled a grunt as he was dragged across the alpha's lap, to a position that was, unfortunately, all too familiar. He tried to drown out the muffled, excited clamor of the other warriors, not wanting to remember that he had an audience. Dean always hated it when Crowley did it in public. 

"So here's what's gonna happen, pretty baby," said the alpha, smoothing his hand over Dean's upturned rump, the callous flesh rough against his smooth, unblemished flesh. "I'm gonna spank you ten times for each time you hit me. Can you tell me how much that is?"

Dean refused to respond, not wanting to humor the alpha's patronizing tone. The hand smacked him sharply on his left cheek, causing an whoop from the surrounding warriors.

"Answer me, princess." 

"Okay, fine!" Dean barked, pausing to do some mental calculations. Three times where his kidney should have been, once in the crotch, and once in the nose... "F-fifty?"

It was a big number, but Dean had had worse. That Abbadon bitch was a sadist.

"You got it, pretty baby." Dean gritted his teeth at the grin in the alpha's voice. "So here's what's gonna happen: you're gonna count each one of 'em for me, and then you're going to say 'daddy.' As in, 'One, Daddy. Two, Daddy. Three, Daddy.' And so forth. You got that?" 

Dean grit his teeth. It wasn't enough that this dick had beaten him without breaking a sweat, taken away his one chance at freedom, he had to make this as drawn-out and humiliating as possible?

"Fuck you," Dean ground out. "I'm not doin' that." 

"Now, that's no way to speak to Daddy," the alpha grinned, delivering five hard smacks in quick succession while the others hooted and jeered their approval. "You will do that, and what's more, each one you DON'T do that? Don't count." He smoothed his hand once more over the pinkening flesh. "Now what do we say."

Dean grimaced. He didn't want to do this. He wanted to be back in his stupid plush dog bed, pretending not to listen to Crowley's crumby reality TV shows and trying to forget this had ever happened. But the alpha's hold on him was firm, and Crowley had yet to do anything to try and put a stop to the situation. All Dean could do was take it. "Yes, fine, I'll do it."

The warrior leaned in close. "Yes, what?" 

Dean's ears burned. "Yes, *Daddy.*" 

He could feel the alpha grinning, breath hot against his ear. "Atta girl."

Dean could feel his face burn hotter still, flush turning bright scarlet across his cheeks and neck, as the alpha pulled his panties down beneath plush ass cheeks. People had seen him in worse positions before, of course, but that didn't make the indignities any more palatable. 

He squeezed his eyes shut, the tension in the air palpable as he waited for the alpha to strike his first blow. Then he did, massive palm striking firmly across the plump, freckled cheeks. A veritable cheer went up among the other warriors, obviously quite content to watch the show. 

"One," Dean ground out, despair filling him as he realized this was just the beginning. "Daddy."

The spanking continued, the other warriors offering a colorful commentary between each resounding smack:

"Yeah, smack that pretty ass red!"

"Teach that cute little bitch a lesson." 

"Show her what she's good for!" 

By the time they'd reached forty, Dean was sniffling steadily, hot tears trailing freely down his cheeks without the use of his hands to stop them. The words came out as wrecked, barely strung together syllables, and he missed a solid ten counts due to nothing more than how hard he was crying. 

By the time they'd reached fifty, his ass was nearly glowing tomato red.

The alpha finally let him sit up, pulling him close in a sickening parody of tenderness. What was worse was that Dean couldn't help but lean into the affection, even if it was feigned: it was the same reason why he leaned into Crowley's every touch, letting him pet his hair while he knelt beside him at the table or sucked him off, so starved he was for genuine love and kindness in his life. 

"Hush now," the alpha crooned, using the back of his finger to dry Dean's tears. "Don't cry, pretty baby." It occurred to Dean belatedly that he'd let go of Dean's hands, but he was still too wrecked to anything about it. They'd gotten him good. "You're punishment's over."

Dean felt a small, temporary relief at this, but it was short lived: his stomach grew cold as he felt the alpha grin against his ear, meaty hand snaking down the front of his lace panties. He didn't have to look up to feel the hunger in the alpha's eyes, see his predatory smile. 

"Now, the REAL fun can begin."

**Notes for the Chapter:**

> Drop some comments, kudos, and suggestions!


	4. The Climax

Dean was only fifteen years old when they'd categorized him as a pleasure slave, and he was sixteen when he began training with Abaddon. He'd been full of fight then, all spit and vinegar, a raging, strong-willed buck who'd railed against his station at every turn, determined to prove that they were wrong in their selection. If he just gave them enough trouble, he thought, they'd have no choice but to grant him a reevaluation. 

She'd beaten most of the fight out of him pretty damn quickly.

"C'mon, little boy," Abaddon had crooned, towering over her kneeling charge in six-inch stilettos. "Beg for me. Beg for your Mama, and this can all go away."

Dean grit his teeth, arms straining at the bonds that held his wrists behind his back. "Like hell I will, ginger bastard." 

Abaddon merely clucked her tongue -- infuriatingly, she had proved almost impossible to provoke -- and lifted one stiletto to between his shoulder blades, shoving him face-first to the ground so that his lace-framed ass was in the air. The crisp *thwack!* of her riding crop collided with the bare, bruised flesh of his cheek, making him jolt.

The deceptively soft leather tip came down to rest on his overfull balls, the cock ring keeping him perpetually on the cusp of release. "Wanna try that again, little boy?" 

Dean stifled a whimper. "Go to hell," he whispered, the quiver in his voice betraying his desperation. He braced himself for the crack of the crop against his sensitive balls, but none came. Instead, he felt the smooth leather caress them gently through the precum-dampened material, angling strategically forward to brush the aching length of his cock. 

Dean couldn't help it: he started to cry, fat, silent tears cascading down his pinkened cheeks. He needed to come so badly, he felt like he could die: it had been a solid six months since he'd been allowed a decent orgasm, and he was only milked a couple times a month now. 

"You wanna come real bad, don't you, baby?" Abaddon cooed, voice soft and understanding. It was a caricature of maternal love, but Dean would take it. He'd take whatever affection he could get. "It's been such a long time, hasn't it?"

Dean nodded as best he could, thighs trembling as the crop continued it's gentle assault. 

Abaddon clucked her tongue. "Oh, you poor little thing. Don't worry baby, Mama's gonna make it all better: by the end of the day, I'll make you come all over my nice soft titties, and you'll even get to lick it up afterwards. That sound good to you, baby?"

Dean didn't at all like the idea of licking up his own cum, but he didn't have much of a say in the matter: he needed to get his release, and anyway, it wasn't the first time he'd been made to do such a thing. 

"Maybe afterwards, if you're very very good, I'll even give you a bath," Abaddon postulated, still keeping her voice soft and gentle, almost loving. "You'd like that, wouldn't you baby?"

Dean tried to nod again. He would. God, he would. He knew it was all a cruel game, a means of playing with his head and fooling him into subconsciously granting her his trust, but no one ever touched Dean that way: gentle hands stroking his hair, and index finger caressing his temple, a warm palm rubbing his back. Since he'd been sold, the adults surrounding him had treated him like an animal bred for slaughter, and he hadn't realized how much he'd missed being touched the way she touched him then. 

She knew how to make him feel loved, cared for, even when every part of him knew it was a trick. And that was the weapon she would use to break him. 

"Yeah. Yeah, you would, wouldn't you." Dean could hear her smile, see the curl of her ruby red lips, and he wanted to hate her. He wanted to. "You just gotta do one thing for Mama, and then I'll give you everything you need." She leaned in close, so much so that Dean could feel those grinning lips brushing the shell of his ear. "Beg." 

Dean felt it the very instant he cracked. 

***

"Please! Please, please, oh God please!" 

It had been two years since then and Dean was having no trouble begging now, hips thrusting into the air and hard cock bobbing as the beta warrior's hands retreated and cut off his release for the third time. The other warriors laughed at jeered at the spectacle, predictably delighted to see him debase himself further. 

The alpha grinned against his ear, still holding Dean strong against his chest, both wrists pinched firmly behind Dean's back. "You know what you gotta say to make it stop, little girl," he chuckled. "Just five little words to start with. C'mon, you can do it."

Dean thumped his head back against the scarred chest in frustration, a high whine tearing itself from his throat. 

"No? Alrighty, then: one more round, Earl. She's bound to crack sooner or later." 

The beta -- Earl, apparently -- resumed his ministrations on Dean's slick, purpling cock, while the others resumed their boisterous running commentary. 

"Yeah, work that little pink prick," someone grunted, furiously jacking his own member. 

"It ain't a prick," someone else spat. "Little girls like that don't have pricks, dumbass. That right there's a clit."

"A nice little clit for a nice little girl," a third party chimed in. 

Dean's eyes screwed shut. He was too far gone for it to register now, but he knew the shame of the warriors' words would catch up with him. It might be hours or days before it hit him, but something told Dean it would be a long, long time before he could look in the mirror again. 

He let out a choked sob as the meaty hand retracted once more, his poor dick pulsing forlornly in time with his heart. 

"Got anything to say, babydoll?" the alpha inquired, cheekily plucking at a nipple beneath the thin, lacy fabric of Dean's dress. 

"I wanna come," Dean wailed, triggering another roar of laughter at his misery. 

"Yeah, I think we gathered that, doll. I mean, do you have anything you wanna tell us?" 

Dean bit his lip. He knew what the alpha wanted him to say, and he felt the exact moment he cracked.

"I'll never be a warrior," he recited, quickly and shakily, as though he might burst into hysterics at any second. "I'll never be a warrior 'cause I'm just a little pleasure toy, a little doll for daddies to play with and dress up and take for walks. I'm not a warrior, I'm not a man, I'm just a pleasure slave Oh, PLEASE JUST LET ME FUCKIN' CUM! PLEASE, I'LL DO ANYTHING!" 

"Okay, baby, okay," the alpha chuckled, as though humoring a favorite child. "What princess wants, princess gets." He looked to the beta. "Earl: let her come." 

Earl jacked him off quicker this time, surer. He came almost instantly, head falling back against the alpha's chest and back arching as his eyes fluttered back, hot cum spurting over his chest as he briefly blacked out from pleasure.

When he came to, the warriors were arranging themselves around him in a circle. He barely had time to register the shame of what he'd just done before it occurred to him Crowley was speaking. 

"Remember, boys," he drawled lightly. "Feel free to candy coat him, but no fucking. I like to keep my little toy nice and tight."

Dean barely had time to process what was happening, but somehow, it didn't surprise him: the warriors were jerking off, aggressively, the closest with their cocks mere inches from his face. He barely managed to close his eyes before the first stream of hot cum struck his forehead, dribbling wetly down his nose. The next glob hit his jawline, and the next, his chest. One even dared to rub the tip of his spent cock against his cheek, spreading around the semen, before the alpha shoved him away. 

By the time they were through, Dean was virtually covered in globs of white cum. He'd never felt so utterly dirty, not since the first time they'd told him he'd be a pleasure slave to begin with.

All he could do was sob in overwhelmed, overstimulated shame as the alpha grabbed his hips and began working his frilly pink ass up and down, using him to rub against the tree trunk of his cock. He tried to block out the disgusting, guttural sounds in his ear, but it proved impossible: he could feel the hot wheeze of the alphas breath in his ear, moist and foul, like some rabid animal. 

It only took a few moments for the alpha to come, wet heat blossoming between the cheeks of Dean's ass. The alpha let him go lax against him, still panting in his ear like a dog in the middle of a rut. 

"Damn, that's a good lay," he huffed out, voice the contented sleepiness most people get after a pleasant Thanksgiving dinner. He grinned tiredly against Dean's ear. "Let me know if you ever forget what you are again, kid. Daddy'll be glad to remind you." 

Dean could only sit there, eyes scrunched shut, the alpha's flacid dick still nestled between his ass cheeks.

Finally, to his unspeakable relief, he heard the door creak open. "Alright, boys. Playtime's over," came Crowley's familiar drawl. "And no 'buts' about it, or someone's getting the shock collar."

**Notes for the Chapter:**

> I'm so sorry. I don't know why I do this to characters I like. As always, feel free to drop kudos, comments, or suggestions (or yell at me.) Next chapter is when things start getting better for Dean, I swear.


	5. The Rescue

**Summary for the Chapter:**

> While waiting for Crowley outside of an outdoor cafe, Dean is approached by an angel.

Dean sat, shivering, on the sidewalk of the outdoor cafe, knees drawn up into his chest and leash attached to the metal chair. Around him, several patrons stared openly, smirking or whispering or taking pictures on their cellphones. Dean knew why: his only clothing today was a pair of frilly pink underwear, the ones Crowley said "looked darling" on him when he was blushing, and of course, he hadn't bothered protesting. Through it, you could just see the outline of his cock cage.

It had been over a year since Dean had been made to "fight" the warriors, and he'd never dared to complain about his station again. Sometimes it felt as though Crowley was purposefully provoking him, giving him increasingly impossible or humiliating tasks to complete, but Dean always kept quiet and went about them dutifully. 

Sometimes, it helped to pretend he was an object without a will or a mind of his own. Sometimes he wished he was one. Objects, after all, felt no shame, and the shame Dean felt during some of Crowley's tasks threatened to eat him from the inside out. 

But there was nothing he could do about it. This was his life, and for the foreseeable future, it was the only life he'd ever have. He'd long since accepted that.

"Excuse me, young man," came a concerned, gravely voice. "Could I offer you my coat?"

Dean blinked in surprise, and looked up to see an angel. Or at the very least, a person who very much resembled one. 

He had soft, striking blue eyes and a shock of wild blackish hair, skin flawlessly tan and a jawline textured with stubble. The coat in question was an Columbo-style khaki trench, a little too large for the man's lithe frame. He looked down at Dean with genuine kindness and concern he hadn't seen in a long, long time. 

Dean swallowed. "Th-thanks, but uh...my master might be mad at me," he stammered, unused to conversing with someone as though they were his equal. 

The man followed Dean's gaze inside, to wear Crowley was still getting his ridiculously elaborate frappucino-type beverage, and then back to Dean again. To Dean's surprise, the man shrugged his coat off of his shoulders, draping it carefully around Dean's. He'd be lying if he said the warmth of the coat wasn't a relief from the chilly weather.

"I will explain to him that I insist," the man assured him. 

Dean could only stare. Who the hell was this guy? He'd had people sympathize with him before -- one sweet old lady once shouted at Crowley that he should be ashamed of himself, and anti-slavery advocates weren't uncommon -- but never like this. You didn't talk to a slave like they were a person. It simply wasn't done.

Things only got weirder when the man sat down beside him --on the GROUND -- and extended his hand. "Castiel Novak," he said, and it took Dean a moment to realize that was the man's name. 

Dean hesitantly shook it, wondering if this was some sort of a test, if he'd be punished for treating a free man with such familiarity. "Um, Dean," he managed. "Winchester, Dean Winchester."

The man -- Castiel -- nodded thoughtfully. "So tell me, Dean: where is your master now?" 

"He's inside," Dean shrugged. Without thinking, he added, "Probably getting one of his froufrou-ass coffee drinks without any actual coffee in 'em."

Castiel's eyes widened slightly, and Dean paled as he realized his mistake. "Oh God, I-I'm sorry, I don't know where that came from -" 

"Your spirit's not broken yet, is it?" Castiel interjected, and Dean was startled by the hint of something in his voice that sounded very much like approval. 

Dean didn't know what to say. If he was being honest with himself, yes, the snarky replies did still spring to mind whenever Crowley spoke, he just trained himself not to say them. He still had dreams, dreams of being free and helping others, he just trained himself not to entertain them. So no, maybe he wasn't quite broken yet. 

"How long have you been a slave, Dean?" Castiel inquired, jogging Dean from his introspection. 

"Since I was four." He answered honestly, without thinking, then added, "That's when I was sold, anyway. I lived at the barracks till I reached the legal age." Castiel nodded, listening intently. Dean paused, questioning briefly whether he should say this, then continued softly. "My, uh. Dad sold me. He said it was for my baby brother to have a future, but I think it's 'cause I looked too much like my mom."

"She...left, I'm presuming?" Castiel postulated. 

Dean shook his head. "Naw. Died, in a fire. Dad didn't like to think about her after that."

"I'm sorry." 

"S'alright," Dean shrugged. Warming to the subject now, he continued, "For a while I wanted to be a warrior. Warriors, it's a position of value: you protect somebody important for ten or twenty years, and you do a good job of it, you get your freedom. Even after I got sorted as a pleasure slave, I couldn't stop thinkin' about that, thinkin' what it would've been like to be free, see little Sammy again and find out what happened to him." Dean looked down at the sidewalk, watching a rogue ant scurry along with a crumb in its mouth. "Crowley must've figured it out somehow, 'cause he put a stop to that pretty quick."

"What did he do?" Castiel inquired, sounding concerned.

"He, uh," Dean forced a smile, trying to convince himself that with hindsight, the experience could be viewed as humorous. "He shoved me in the enclosure with ten or twenty warriors, wearing nothin' but this tiny little satin dress and lace panties." Dean huffed out a nervous chuckle. "Let 'em go to work on me for about two hours." 

Castiel just stared at him. "That's terrible." 

Dean shrugged, still attempting to appear flippant. "If I'd been able to fight the guy like I was supposed to I would've been okay. I just didn't stack up, is all."

Castiel shook his head, brow pursed in a frown. "Warriors go through years of intensive training, Dean. It wasn't fair for him to hold you to that standard."

Dean swallowed, feeling oddly emotional to hear someone side with him. He nodded quietly, staring down at the sidewalk.

Castiel, thankfully, seemed to notice his discomfort and decided not to dwell on the subject. "So tell, me, Dean. What would you do if you weren't a slave?" 

Dean was perplexed. Why was this guy asking him this? Nevertheless, he considered it. 

"I'd wanna help people," he decided. "Kids, in bad situations. Maybe some sort of therapy." A pause. "And I'd sleep in my own bed, a real bed. And I'd eat at a table, and I'd spend time with my brother Sammy. And I'd read more." 

Castiel nodded. "You like to read, do you?"

"Yeah. I never got much of an education, but I knew the alphabet, and that was all I really needed to teach myself. Taught a few little kids back at the barracks, too." He paused, and looked around cautiously. "Crowley's got shit taste in literature, between you and me, but he's got a few Vonnegut books that I can't put down. Slaughterhouse 5? Cat's Cradle?" Dean chuckled. "That shit's my jam, man." 

Castiel nodded thoughtfully, but remained silent. 

Dean was surprised by how much he didn't want the conversation to end. "So what about you, Cas?" he prompted, not even registering the nickname as it slipped off his tongue. "What do you do?"

Cas blinked, and opened his mouth as if to answer, when a familiar voice cut in. "What have we hear? Someone tinkering with the merchandise?" 

The British accent grated its way to the base of Dean's spine. Of course Crowley would ruin the first actual conversation he'd had with another human being in years.

By Castiel's death glare, he didn't feel any more warmly. "I take it you're Crowley," he grumbled, brushing off his suit as he got to his feet. 

"Delighted," Crowley purred, barely acknowledging him as he strolled around the table to take his seat, "froufrou-ass" coffee drink in hand so big that they could have easily named a planet after it. "Dean, take off that gaudy thing, will you? Then get over here and put that mouth of yours to good use." 

Dean's heart sunk. He knew Crowley meant cockwarming, and though Dean was used to it, he really, really didn't want to do it in front of Cas. He didn't want Cas to see him as the same low, pathetic slut that everyone else did. 

Nevertheless, he had no choice but to comply, carefully shrugging off the khaki trench coat and draping it over the back of a chair. His face was already turning pink as he crawled towards Crowley, not daring to look at Cas as he moved to do his duty. 

"I don't think that will be necessary," Cas interjected coolly, and nothing could have prepared Dean for the next words that came out of his mouth. "I'd like to buy him."

**Notes for the Chapter:**

> Next chapter should be the last, but I'm considering doing some smutty time stamps from Dean's time as a sex slave and subsequent relationship with Cas (which, I assure you, will be plenty kinky in its own right.) I will be taking requests when it comes to those, so feel free to hit me up with suggestions!


	6. The Epilogue

**Summary for the Chapter:**

> Years later, Dean adapts to the joys and tribulations of life as a free man.

Dean's eyelashes fluttered as he arched off the bed, Cas's soft lips the sweetest torment as he gently, slowly kissed his way down the firm expanse of Dean's chest, suckling his rosy red nipples. 

All the while, his hand rubbed him gently through the lace fabric of his underwear, keeping him perpetually aroused while never tipping him over the edge. 

Sex with Cas was different from anything Dean had ever experienced, in predominantly two ways: the first was that everyone else who had ever slept with him, Dean realized, had used him in some way. Cas never used him. He worshiped him, cherished him, and made it clear before and after every session that Dean – despite being the one usually trussed up in panties and fuzzy handcuffs – was the one in control. Which lead to the second point, which was that Dean could call off the sex whenever he chose to do so. 

Cas kissed his way down Dean's soft belly, making him squirm as warmth pooled inside of him. Cas looked up through his eyelashes as he worked his way closer to the pinkened cock protruding from his panties, and that sight alone was almost enough to make him come right then and there. 

Dean writhed like a snake against his lace bonds as he watched Cas free his member, tracing the pulsing length lightly up and down with his slender fingertips, peppering kisses to its length and head. 

“Cas,” Dean groaned, hips gyrating uselessly in an attempt to get relief. 

“Yes, Dean.”

He thumped his head back against the pillow as a thumb rubbed a torturous circle around the purpling head. “Please, let me come!” 

“Soon, Dean. Soon,” Cas assured him, resuming his sensual torture on Dean's prick, watching as he writhed and arched on the bed, muscles taught and eyes rolling, mouth lolling open in a silent 'o.' “You've been so good for me, Dean. So very beautiful.” He dropped a final kiss to the head of Dean's cock. “Come whenever you like.” 

Dean barely had a chance to respond before Cas had taken his entire length into his mouth, deep-throating his whole in one smooth swoop. 

Dean nearly blacked out as he came, arching off the bed and wailing out Castiel's name as his cock pulsated into the warm suction of his throat. 

...

"I'd like to buy him." 

Those were the five words that had changed his life. 

He was still in shock by the time Crowley snapped out of it, letting out a short scoff. "Sorry, kitten, but I'm afraid I've gotten quite attached to the little darling. We're quite close, you see. Besties, in fact."

"I'm sure I could pay you more than enough to compensate for such a devastating loss," Cas monotoned, and if Dean hadn't still been so stunned, he might have snorted. "Frankly, I could pay you more than you could possibly imagine." 

"I can imagine quite a bit, sunshine."

Castiel opened his mouth as if to argue, then closed it again. "I don't believe we've been formally introduced, Crowley," he said coolly. 

"A travesty."

"I am Castiel." 

"Fascinating."

"Novak." 

That last word caused Crowley to pause mid-sip of his froufrou coffee beverage, eyes going almost comically wide. Though Dean, at the time, was oblivious to the name's meaning or the weight it carried, the Novak family was the fifth richest family in America, ninth richest in the world. Castiel, as Dean would later discover, lived a comparatively humble lifestyle, but he wasn't opposed to throwing his name around when the situation called for it. 

"Please excuse me, Mr. Novak," Crowley murmured, finally, as he fumbled to retrieve his cellphone. "I need to retrieve Dean's necessary papers." 

With that, he staggered away, frantically dialing numbers, and leaving behind a smug Castiel and a thoroughly confused Dean. Cas watched him go before returning his attentions to his new charge. 

"As I was saying earlier, before we were...interrupted," he sighed, draping his coat back over Dean's shoulders. "I'm an attorney, specializing in advocacy against the practice of slavery. I've long since realized that I can't do it for all of them, but when I meet a slave in a particularly bad situation, I make it a point to personally ensure that they are freed and cared for. Due to your age and absence of reliable family connections, I'll presume that you lack income, so I'd be glad to provide you with a home and resources for the foreseeable future. But rest assured, your papers will be nullified as soon as possible."

Dean stared. This couldn't possibly be happening. It couldn't. "I-I don't understand," he managed. 

"You're going to be freed, Dean," Cas reiterated. "I'll see to it that you're provided with opportunities for suitable education, and that you have a chance to see your brother. I reside with several other freed slaves of various backgrounds, including Miss Charlie Bradburie, Mr. Benny Lafitte, Mr. Kevin Tran and his mother, Mrs. Tran, as well as several children I helped to liberate from the barracks via legal technicalities. I'm certain you will all get along." 

Dean didn't know how to process this. It was too much. There was no way it could possibly be happening, yet something told him it wasn't a dream. 

He was hit with the overwhelming urge to show his gratitude, which he instinctively did the only way he knew how: he went for Castiel's zipper. 

Just as he was shimmying towards his target, however, he was halted by firm, gentle hand on his forehead.

"Dean," said Cas, tone miraculously unsurprised. "What are you doing?"

"I-I wanted to thank you," Dean explained, not sure what to make of the rejection. Most people within Crowley's social circle had used him in one way or another, and certainly no one had ever turned down Crowley's offers for him to perform oral sex before.

Castiel scowled slightly. "Dean, please understand: I am not purchasing you for the purposes of sex. I am purchasing you exclusively to free you. It's not that I find you undesirable or unattractive in the slightest, but I consider sexual relations between slave and proprietor to be an act of rape. Do you understand?" 

Dean nodded hesitantly, feeling his ears turn pink. He felt somewhat foolish now that his attempt at gratitude had been rejected, and he hoped desperately that it wouldn't negatively impact Castiel's view of him. 

He wished he could articulate how firmly ingrained it was that his body was the only thing he had to offer, how many times he'd been reduced to an object, a receptacle for the pleasure of others. He still wanted to thank Cas, but he didn't know how. He didn't have anything to offer except for a warm hole. 

Castiel rested a comforting hand on his shoulder, and Dean, on instinct, leaned into the touch.

"You're a beautiful person, Dean," Castiel assured him gently, and Dean felt as though his insides could melt at the praise. No one had ever said something like that to him before. Not like that, anyway. "I could tell by the way you spoke of your aspirations, the way you spoke of your brother. I can say with certainty that you have a truly beautiful soul." 

Dean let his eyelids flutter. He swallowed wetly, but he willed himself not to cry: he'd already done enough of that for one day. "Thank you," he whispered. 

Once again, they were interrupted by Crowley's return, though this time, for whatever reason, it didn't bother him quite so much. 

"His papers will be arrive this evening, Mr. Novak," Crowley announced. It was jarring to hear him so subservient. "Until then, you can consider him good as yours." 

...

Dean was now twenty-six years old. Healing was an ongoing process, but with the help of his therapist, Missouri, (who, ironically enough, he'd once insisted to Cas he hadn't needed) things were going predominantly well. 

It had taken him a while to catch up with his education, but he was now pursuing a degree in a psychology, aspiring to help kids in situations similar to his own. Castiel had been very supportive of that, pointing to how good he was at talking to the freed slave children who lived with them, Ben, Claire, and Alex, even talking Ben down from panic attacks on several occasions. 

Moreover, he'd finally gotten to see Sammy again, though Missouri had somehow convinced him and Cas to wait a while after he was freed to track him down. 

"I've had a lot of clients who were liberated from slavery, and their families don't always greet them with open arms," she'd explained. "There can be a lot of misplaced guilt and anger involved, a lot of self-justification. It can be crippling to the freed person's healing process." 

So, Dean decided to play it safe, and waited. And though he knew Missouri was very justified in her reasoning, he now wished he hadn't. Sam no longer spoke to John, for the reasons that he'd sold Dean and also because John was, broadly speaking, an emotionally abusive dickbag. 

He'd lived with Bobby since he was sixteen, refusing to touch any of the money garnered by Dean, and as it turned out, he didn't need to: he'd gotten a free ride to Princeton, where he intended to study law and eventually become an anti-slavery advocate. Cas had already promised him a place in his firm. 

As for Dean, he'd found himself suddenly surrounded by people who genuinely cared about him -- Sam, Bobby, his wife Ellen and daughter Jo, Missouri, and of course, Cas and his extended family of freed slaves -- and sometimes he still didn't know what to make of it. He occasionally went through periods of intense depression, in which, against all logic and reason, he thought it was all some elaborate trick, that they were only pretending to love him and care for him to gain his trust, like Abaddon.

Missouri had assured him that this was a normal, if unfortunate, part of the process, and that with time and support it would get better. 

With time, he'd learned to stop feeling ashamed of his body and the way he looked, learning to take pride in his appearance and covet his collection of three-piece suits. And yes, he also did enjoy the odd pair of pink satin panties. It made him feel a tad uncomfortable to find himself drawn to the article of clothing that had been used to degrade him, but he figured the heart wants what it wants.

Which, of course, could also be applied to his love life. 

It had taken a long, long time for Cas to become comfortable with embarking in a romantic relationship with Dean, not wanting to take advantage of the confused feelings of a freed slave over a decade younger than himself, who, in spite of his extended sexual history, had no actual romantic experience. But years went by, and Dean was grew more sure than anything that he'd only ever want Cas. 

Eventually, it became clear that Cas would only ever want him, too.

Dean's enduring predilections towards BDSM, and sex that most people would consider to be degrading, had thrown them both for yet another loop, yet Missouri had assured them that it was perfectly natural.

"Sexual fetishes are often the brain's way of working out trauma," she'd told them. "If a person's parents shamed him for wearing diapers, he might enjoy being forced to wear them by an authoritative figure. If a man had a domineering mother, he might come to like being dominated by women. I see nothing wrong with entertaining Dean's fantasies, as long as things are kept safe, sane, and consensual."

Dean wasn't sure how he'd felt about being compared to Diaper Dude and Oedipus Guy, but part of him was intensely relieved to know that his inclinations were normal.

And at the end of it all, nothing was quite comparable to moments like these, when he lay in bed, shivering as his heart rate slowed, while his Cas, his personal guardian angel, tucked the blankets around him and kissed the back of his neck and told him how beautiful and good he was. 

He knew that eventually the soft blanket of night would be drawn back, and every one of his challenges would be waiting for him come morning. But now, he was with Cas, sleeping in a real bed, with a person who actually loved him. And moments like these stretched on forever, eternities in and of themselves, just for them.

**Notes for the Chapter:**

> So this is it, y'all! Though I felt guilty about torturing poor, sweet Dean, this was a lot of fun to write, and your comments brought me indescribable joy. I can't help but wonder what the readers of my extremely fluffy public account would think if they knew what kind of kinky shit I get up to under the veil of anonymity. 
> 
> I'll soon start adding some timestamps about this, mainly smutty stuff and kink exploration about Dean's time as a sex slave, so HIT ME UP WITH REQUESTS IN THE COMMENTS! Got a specific kink you'd like to see fulfilled, or a loose end you'd like to see tied up? Want to see Dean confront John, or reunite with Sam and Bobby? You know what to do! Shoot me a comment, and I'll do my best to fill it.

**Author's Note:**

> Drop by in the comments and let me know what you think!


End file.
